NPASS Compound

Structure

NPC98115 OpenBabel07101719152D 29 30 0 0 0 0 0 0 0 0999 V2000 -4.3301 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 14 1 0 0 0 0 2 14 1 0 0 0 0 3 15 1 0 0 0 0 4 15 1 0 0 0 0 5 29 1 0 0 0 0 6 12 1 0 0 0 0 6 14 2 0 0 0 0 7 13 1 0 0 0 0 7 15 2 0 0 0 0 8 10 1 0 0 0 0 8 16 2 0 0 0 0 9 11 2 0 0 0 0 9 16 1 0 0 0 0 10 17 2 0 0 0 0 11 17 1 0 0 0 0 12 18 1 0 0 0 0 13 19 1 0 0 0 0 16 21 1 0 0 0 0 17 25 1 0 0 0 0 18 22 1 0 0 0 0 18 24 2 0 0 0 0 19 23 2 0 0 0 0 19 24 1 0 0 0 0 20 21 1 0 0 0 0 20 22 2 0 0 0 0 20 23 1 0 0 0 0 21 26 2 0 0 0 0 22 27 1 0 0 0 0 23 28 1 0 0 0 0 24 29 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	396.19
Volume:	426.77
LogP:	6.692
LogD:	3.609
LogS:	-3.603
# Rotatable Bonds:	7
TPSA:	86.99
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.45
Synthetic Accessibility Score:	2.824
Fsp3:	0.292
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.869
MDCK Permeability:	1.4111644304648507e-05
Pgp-inhibitor:	0.73
Pgp-substrate:	0.061
Human Intestinal Absorption (HIA):	0.021
20% Bioavailability (F20%):	0.887
30% Bioavailability (F30%):	0.243

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.007
Plasma Protein Binding (PPB):	96.3778076171875%
Volume Distribution (VD):	1.469
Pgp-substrate:	4.714828968048096%

ADMET: Metabolism

CYP1A2-inhibitor:	0.635
CYP1A2-substrate:	0.286
CYP2C19-inhibitor:	0.914
CYP2C19-substrate:	0.065
CYP2C9-inhibitor:	0.901
CYP2C9-substrate:	0.916
CYP2D6-inhibitor:	0.596
CYP2D6-substrate:	0.233
CYP3A4-inhibitor:	0.36
CYP3A4-substrate:	0.153

ADMET: Excretion

Clearance (CL):	12.98
Half-life (T1/2):	0.195

ADMET: Toxicity

hERG Blockers:	0.037
Human Hepatotoxicity (H-HT):	0.831
Drug-inuced Liver Injury (DILI):	0.737
AMES Toxicity:	0.019
Rat Oral Acute Toxicity:	0.346
Maximum Recommended Daily Dose:	0.107
Skin Sensitization:	0.852
Carcinogencity:	0.145
Eye Corrosion:	0.003
Eye Irritation:	0.353
Respiratory Toxicity:	0.608

Download Data

Data Type	Select
General Info & Identifiers & Properties
Structure MOL file
Source Organisms
Biological Activities
Similar NPs/Drugs

Natural Product: NPC98115

Natural Product ID:	NPC98115
*Common Name:**	Vismiaphenone D
IUPAC Name:	[2,6-dihydroxy-4-methoxy-3,5-bis(3-methylbut-2-enyl)phenyl]-(4-hydroxyphenyl)methanone
Synonyms:	Vismiaphenone D
Standard InCHIKey:	FKLXSDINWGPHEI-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C24H28O5/c1-14(2)6-12-18-22(27)20(21(26)16-8-10-17(25)11-9-16)23(28)19(24(18)29-5)13-7-15(3)4/h6-11,25,27-28H,12-13H2,1-5H3
SMILES:	COc1c(CC=C(C)C)c(O)c(c(c1CC=C(C)C)O)C(=O)c1ccc(cc1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL463208
PubChem CID:	5675
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000120] Benzophenones

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO9701	Vismia cayennensis	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9917284]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
EC50	1
IC50	1

Activity Type	# Activity
Cell Line	1
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT315	Cell Line	CEM-SS	Homo sapiens	IC50	=	30.0	ug.mL-1	PMID[490699]
NPT1114	Organism	Human immunodeficiency virus	Human immunodeficiency virus	EC50	=	11.0	ug.mL-1	PMID[490699]

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available in NPASS)

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

● The left chart: Distribution of similarity level between NPC98115 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	345
0.1-0.2	1544
0.2-0.3	3994
0.3-0.4	10539
0.4-0.5	7723
0.5-0.6	3615
0.6-0.7	5978
0.7-0.8	5408
0.8-0.85	1986
0.85-0.9	955
0.9-0.95	488
0.95-1	122

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC186838
1.0	High Similarity	NPC274109
1.0	High Similarity	NPC12165
1.0	High Similarity	NPC477244
1.0	High Similarity	NPC168105
1.0	High Similarity	NPC25287
1.0	High Similarity	NPC477243
1.0	High Similarity	NPC1486
1.0	High Similarity	NPC41461
1.0	High Similarity	NPC66349
1.0	High Similarity	NPC477242
1.0	High Similarity	NPC249606
1.0	High Similarity	NPC150399
0.9924	High Similarity	NPC317119
0.9924	High Similarity	NPC153979
0.9924	High Similarity	NPC472419
0.9923	High Similarity	NPC13575
0.9923	High Similarity	NPC131039
0.9923	High Similarity	NPC156092
0.9848	High Similarity	NPC21350
0.9846	High Similarity	NPC103842
0.9846	High Similarity	NPC286336
0.9774	High Similarity	NPC472366
0.9774	High Similarity	NPC477956
0.9774	High Similarity	NPC470211
0.9769	High Similarity	NPC139813
0.9769	High Similarity	NPC175098
0.9769	High Similarity	NPC27643
0.9769	High Similarity	NPC20560
0.9769	High Similarity	NPC192304
0.9769	High Similarity	NPC56031
0.9769	High Similarity	NPC144051
0.9769	High Similarity	NPC18877
0.9769	High Similarity	NPC472365
0.9769	High Similarity	NPC28753
0.9769	High Similarity	NPC294593
0.9769	High Similarity	NPC159623
0.9769	High Similarity	NPC263670
0.9769	High Similarity	NPC337373
0.9769	High Similarity	NPC312318
0.9769	High Similarity	NPC204960
0.9769	High Similarity	NPC82225
0.9769	High Similarity	NPC242294
0.9769	High Similarity	NPC188646
0.9701	High Similarity	NPC11056
0.9701	High Similarity	NPC80962
0.9701	High Similarity	NPC326109
0.9701	High Similarity	NPC172250
0.9701	High Similarity	NPC213659
0.9701	High Similarity	NPC48624
0.9701	High Similarity	NPC259166
0.9701	High Similarity	NPC144118
0.9701	High Similarity	NPC204985
0.9701	High Similarity	NPC219917
0.9701	High Similarity	NPC215311
0.9699	High Similarity	NPC251681
0.9699	High Similarity	NPC243528
0.9699	High Similarity	NPC471620
0.9692	High Similarity	NPC205468
0.9692	High Similarity	NPC212631
0.9692	High Similarity	NPC129132
0.9692	High Similarity	NPC257756
0.9692	High Similarity	NPC87231
0.963	High Similarity	NPC321980
0.963	High Similarity	NPC110969
0.963	High Similarity	NPC469404
0.963	High Similarity	NPC470089
0.963	High Similarity	NPC55832
0.963	High Similarity	NPC470087
0.963	High Similarity	NPC26051
0.963	High Similarity	NPC52789
0.963	High Similarity	NPC268204
0.9627	High Similarity	NPC295384
0.9627	High Similarity	NPC283429
0.9615	High Similarity	NPC112192
0.9615	High Similarity	NPC189106
0.9615	High Similarity	NPC66384
0.9615	High Similarity	NPC308037
0.9615	High Similarity	NPC186097
0.9615	High Similarity	NPC313618
0.9615	High Similarity	NPC128348
0.9615	High Similarity	NPC164236
0.9615	High Similarity	NPC475008
0.9615	High Similarity	NPC64359
0.9615	High Similarity	NPC309717
0.9615	High Similarity	NPC262359
0.9615	High Similarity	NPC475009
0.9559	High Similarity	NPC226636
0.9559	High Similarity	NPC11561
0.9556	High Similarity	NPC69769
0.9556	High Similarity	NPC253822
0.9556	High Similarity	NPC101366
0.9556	High Similarity	NPC261227
0.9556	High Similarity	NPC241100
0.9556	High Similarity	NPC159275
0.9556	High Similarity	NPC270883
0.9556	High Similarity	NPC172986
0.9552	High Similarity	NPC124269
0.9552	High Similarity	NPC472368
0.9549	High Similarity	NPC472364
0.9549	High Similarity	NPC213603
0.9549	High Similarity	NPC472367
0.9549	High Similarity	NPC473391
0.9549	High Similarity	NPC476333
0.9549	High Similarity	NPC24394
0.9545	High Similarity	NPC164136
0.9542	High Similarity	NPC215875
0.9542	High Similarity	NPC15834
0.9489	High Similarity	NPC475705
0.9489	High Similarity	NPC106985
0.9489	High Similarity	NPC310130
0.9489	High Similarity	NPC245482
0.9489	High Similarity	NPC476178
0.9489	High Similarity	NPC39329
0.9489	High Similarity	NPC143896
0.9489	High Similarity	NPC166138
0.9489	High Similarity	NPC75049
0.9489	High Similarity	NPC175504
0.9489	High Similarity	NPC18585
0.9489	High Similarity	NPC51887
0.9489	High Similarity	NPC221432
0.9489	High Similarity	NPC169591
0.9489	High Similarity	NPC68104
0.9489	High Similarity	NPC164980
0.9489	High Similarity	NPC150408
0.9489	High Similarity	NPC117836
0.9489	High Similarity	NPC301751
0.9489	High Similarity	NPC257097
0.9489	High Similarity	NPC91560
0.9489	High Similarity	NPC149026
0.9485	High Similarity	NPC3188
0.9485	High Similarity	NPC64908
0.9485	High Similarity	NPC147688
0.9485	High Similarity	NPC26238
0.9485	High Similarity	NPC282300
0.9485	High Similarity	NPC118840
0.9485	High Similarity	NPC205006
0.9485	High Similarity	NPC103362
0.9485	High Similarity	NPC156590
0.9481	High Similarity	NPC216978
0.9481	High Similarity	NPC96565
0.9481	High Similarity	NPC303633
0.9481	High Similarity	NPC301217
0.9481	High Similarity	NPC53181
0.9481	High Similarity	NPC217186
0.9481	High Similarity	NPC55018
0.9481	High Similarity	NPC18260
0.9481	High Similarity	NPC220062
0.9481	High Similarity	NPC78913
0.9478	High Similarity	NPC303644
0.9478	High Similarity	NPC209560
0.9478	High Similarity	NPC294409
0.9478	High Similarity	NPC181124
0.9478	High Similarity	NPC162680
0.9478	High Similarity	NPC7013
0.9478	High Similarity	NPC188879
0.9478	High Similarity	NPC23870
0.9478	High Similarity	NPC116632
0.947	High Similarity	NPC16197
0.9462	High Similarity	NPC84772
0.9462	High Similarity	NPC247779
0.942	High Similarity	NPC234629
0.942	High Similarity	NPC311741
0.942	High Similarity	NPC473015
0.942	High Similarity	NPC197252
0.942	High Similarity	NPC328623
0.942	High Similarity	NPC209040
0.942	High Similarity	NPC473013
0.942	High Similarity	NPC236766
0.942	High Similarity	NPC476055
0.9416	High Similarity	NPC167624
0.9416	High Similarity	NPC76338
0.9416	High Similarity	NPC220998
0.9416	High Similarity	NPC228504
0.9416	High Similarity	NPC227579
0.9416	High Similarity	NPC78
0.9416	High Similarity	NPC10937
0.9416	High Similarity	NPC166482
0.9416	High Similarity	NPC223500
0.9416	High Similarity	NPC328164
0.9416	High Similarity	NPC265040
0.9416	High Similarity	NPC177354
0.9416	High Similarity	NPC64915
0.9416	High Similarity	NPC40833
0.9416	High Similarity	NPC1089
0.9416	High Similarity	NPC125855
0.9416	High Similarity	NPC182852
0.9416	High Similarity	NPC296917
0.9416	High Similarity	NPC144499
0.9416	High Similarity	NPC306829
0.9416	High Similarity	NPC66515
0.9416	High Similarity	NPC76372
0.9416	High Similarity	NPC148757
0.9416	High Similarity	NPC32739
0.9416	High Similarity	NPC324134
0.9416	High Similarity	NPC107572
0.9416	High Similarity	NPC297600
0.9416	High Similarity	NPC148545
0.9416	High Similarity	NPC161506
0.9416	High Similarity	NPC37496

Chemically structural similarity: II. Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC98115 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	311
0.1-0.2	965
0.2-0.3	1448
0.3-0.4	2570
0.4-0.5	1985
0.5-0.6	1226
0.6-0.7	442
0.7-0.8	148
0.8-0.85	37
0.85-0.9	12
0.9-0.95	5
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9615	High Similarity	NPD1240	Approved
0.947	High Similarity	NPD1607	Approved
0.9328	High Similarity	NPD1510	Phase 2
0.9281	High Similarity	NPD4378	Clinical (unspecified phase)
0.9143	High Similarity	NPD7410	Clinical (unspecified phase)
0.9124	High Similarity	NPD1549	Phase 2
0.9051	High Similarity	NPD1552	Clinical (unspecified phase)
0.9051	High Similarity	NPD1550	Clinical (unspecified phase)
0.8958	High Similarity	NPD4380	Phase 2
0.8897	High Similarity	NPD7411	Suspended
0.8841	High Similarity	NPD2796	Approved
0.8776	High Similarity	NPD2393	Clinical (unspecified phase)
0.8759	High Similarity	NPD6651	Approved
0.8725	High Similarity	NPD7075	Discontinued
0.8716	High Similarity	NPD8443	Clinical (unspecified phase)
0.8705	High Similarity	NPD2935	Discontinued
0.8671	High Similarity	NPD6799	Approved
0.8649	High Similarity	NPD7096	Clinical (unspecified phase)
0.8649	High Similarity	NPD7819	Suspended
0.8581	High Similarity	NPD6801	Discontinued
0.8521	High Similarity	NPD7421	Clinical (unspecified phase)
0.8456	Intermediate Similarity	NPD1934	Approved
0.8451	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8446	Intermediate Similarity	NPD6599	Discontinued
0.8414	Intermediate Similarity	NPD1511	Approved
0.8411	Intermediate Similarity	NPD7768	Phase 2
0.8411	Intermediate Similarity	NPD3882	Suspended
0.84	Intermediate Similarity	NPD2801	Approved
0.8392	Intermediate Similarity	NPD2800	Approved
0.8387	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8355	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD3750	Approved
0.8333	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.831	Intermediate Similarity	NPD1551	Phase 2
0.8299	Intermediate Similarity	NPD1512	Approved
0.8264	Intermediate Similarity	NPD1243	Approved
0.8258	Intermediate Similarity	NPD6232	Discontinued
0.8239	Intermediate Similarity	NPD2799	Discontinued
0.8239	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.8231	Intermediate Similarity	NPD2533	Approved
0.8231	Intermediate Similarity	NPD2532	Approved
0.8231	Intermediate Similarity	NPD2534	Approved
0.8217	Intermediate Similarity	NPD7473	Discontinued
0.8214	Intermediate Similarity	NPD943	Approved
0.8194	Intermediate Similarity	NPD6959	Discontinued
0.8125	Intermediate Similarity	NPD5953	Discontinued
0.8125	Intermediate Similarity	NPD2344	Approved
0.8121	Intermediate Similarity	NPD920	Approved
0.8117	Intermediate Similarity	NPD3749	Approved
0.8113	Intermediate Similarity	NPD7286	Phase 2
0.8113	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8102	Intermediate Similarity	NPD1203	Approved
0.8095	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8043	Intermediate Similarity	NPD2798	Approved
0.8038	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8038	Intermediate Similarity	NPD6166	Phase 2
0.8038	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8015	Intermediate Similarity	NPD3972	Approved
0.8014	Intermediate Similarity	NPD2654	Approved
0.8013	Intermediate Similarity	NPD5494	Approved
0.8	Intermediate Similarity	NPD5403	Approved
0.7987	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD3817	Phase 2
0.7986	Intermediate Similarity	NPD3748	Approved
0.7943	Intermediate Similarity	NPD2313	Discontinued
0.7937	Intermediate Similarity	NPD3818	Discontinued
0.7929	Intermediate Similarity	NPD6832	Phase 2
0.7919	Intermediate Similarity	NPD7390	Discontinued
0.7914	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7905	Intermediate Similarity	NPD2309	Approved
0.7895	Intermediate Similarity	NPD9493	Approved
0.7883	Intermediate Similarity	NPD9717	Approved
0.7867	Intermediate Similarity	NPD5401	Approved
0.7853	Intermediate Similarity	NPD6559	Discontinued
0.784	Intermediate Similarity	NPD7074	Phase 3
0.7838	Intermediate Similarity	NPD4628	Phase 3
0.7821	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7817	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.781	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD7054	Approved
0.7778	Intermediate Similarity	NPD9545	Approved
0.7778	Intermediate Similarity	NPD3226	Approved
0.7763	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.773	Intermediate Similarity	NPD7472	Approved
0.7722	Intermediate Similarity	NPD919	Approved
0.7714	Intermediate Similarity	NPD1164	Approved
0.7692	Intermediate Similarity	NPD3268	Approved
0.7687	Intermediate Similarity	NPD6100	Approved
0.7687	Intermediate Similarity	NPD6099	Approved
0.7683	Intermediate Similarity	NPD6797	Phase 2
0.7681	Intermediate Similarity	NPD422	Phase 1
0.7676	Intermediate Similarity	NPD4908	Phase 1
0.7669	Intermediate Similarity	NPD5844	Phase 1
0.7662	Intermediate Similarity	NPD7458	Discontinued
0.7647	Intermediate Similarity	NPD1548	Phase 1
0.7643	Intermediate Similarity	NPD5402	Approved
0.764	Intermediate Similarity	NPD3926	Phase 2
0.7636	Intermediate Similarity	NPD7251	Discontinued
0.7635	Intermediate Similarity	NPD2346	Discontinued
0.7625	Intermediate Similarity	NPD1247	Approved
0.7622	Intermediate Similarity	NPD1729	Discontinued
0.7619	Intermediate Similarity	NPD7033	Discontinued
0.76	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD7003	Approved
0.7591	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.759	Intermediate Similarity	NPD7808	Phase 3
0.7589	Intermediate Similarity	NPD1470	Approved
0.7589	Intermediate Similarity	NPD2797	Approved
0.7578	Intermediate Similarity	NPD5710	Approved
0.7578	Intermediate Similarity	NPD5711	Approved
0.7568	Intermediate Similarity	NPD5404	Approved
0.7568	Intermediate Similarity	NPD5405	Approved
0.7568	Intermediate Similarity	NPD5408	Approved
0.7568	Intermediate Similarity	NPD5406	Approved
0.7554	Intermediate Similarity	NPD1610	Phase 2
0.7554	Intermediate Similarity	NPD1201	Approved
0.7534	Intermediate Similarity	NPD230	Phase 1
0.7518	Intermediate Similarity	NPD1876	Approved
0.75	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4308	Phase 3
0.7485	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7457	Intermediate Similarity	NPD4360	Phase 2
0.7457	Intermediate Similarity	NPD4363	Phase 3
0.7452	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7448	Intermediate Similarity	NPD3764	Approved
0.7415	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7415	Intermediate Similarity	NPD1933	Approved
0.7415	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7415	Intermediate Similarity	NPD5124	Phase 1
0.7414	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7414	Intermediate Similarity	NPD4361	Phase 2
0.7407	Intermediate Similarity	NPD1241	Discontinued
0.7394	Intermediate Similarity	NPD3225	Approved
0.7379	Intermediate Similarity	NPD3027	Phase 3
0.7379	Intermediate Similarity	NPD4625	Phase 3
0.7376	Intermediate Similarity	NPD1608	Approved
0.7365	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD1465	Phase 2
0.7343	Intermediate Similarity	NPD3267	Approved
0.7343	Intermediate Similarity	NPD3266	Approved
0.7341	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD1651	Approved
0.7338	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD411	Approved
0.7329	Intermediate Similarity	NPD1296	Phase 2
0.7324	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD6104	Discontinued
0.7312	Intermediate Similarity	NPD2296	Approved
0.7312	Intermediate Similarity	NPD4288	Approved
0.7297	Intermediate Similarity	NPD447	Suspended
0.7293	Intermediate Similarity	NPD9266	Approved
0.7293	Intermediate Similarity	NPD74	Approved
0.7292	Intermediate Similarity	NPD1019	Discontinued
0.7285	Intermediate Similarity	NPD1471	Phase 3
0.7285	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD1283	Approved
0.7247	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD5049	Phase 3
0.7241	Intermediate Similarity	NPD9494	Approved
0.7234	Intermediate Similarity	NPD3847	Discontinued
0.7233	Intermediate Similarity	NPD5890	Approved
0.7233	Intermediate Similarity	NPD5889	Approved
0.7231	Intermediate Similarity	NPD940	Approved
0.7231	Intermediate Similarity	NPD846	Approved
0.723	Intermediate Similarity	NPD4307	Phase 2
0.7218	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7218	Intermediate Similarity	NPD9263	Approved
0.7218	Intermediate Similarity	NPD9267	Approved
0.7218	Intermediate Similarity	NPD9264	Approved
0.7215	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD6798	Discontinued
0.7208	Intermediate Similarity	NPD2354	Approved
0.7203	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7192	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD4662	Approved
0.7179	Intermediate Similarity	NPD4661	Approved
0.717	Intermediate Similarity	NPD6585	Discontinued
0.7163	Intermediate Similarity	NPD4626	Approved
0.7163	Intermediate Similarity	NPD17	Approved
0.7152	Intermediate Similarity	NPD7229	Phase 3
0.7133	Intermediate Similarity	NPD1481	Phase 2
0.7126	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD4287	Approved
0.7123	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7122	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD1613	Approved
0.7114	Intermediate Similarity	NPD3142	Approved
0.7114	Intermediate Similarity	NPD3140	Approved
0.7105	Intermediate Similarity	NPD4477	Approved
0.7105	Intermediate Similarity	NPD4476	Approved
0.7104	Intermediate Similarity	NPD7584	Approved
0.7097	Intermediate Similarity	NPD3295	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD3887	Approved
0.7083	Intermediate Similarity	NPD4749	Approved
0.7081	Intermediate Similarity	NPD6280	Approved

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data